Despite its title, This Will End in Tears: The Miserabilist Guide to Music — a new book from Brooklyn author Adam Brent Houghtaling — posits the idea that sad songs aren’t just for the perpetually gloomy. They’re a dependable place to retreat to during our most melancholic moments and, often, help us to purge our sorrow. They’re also, often, the most intimate way that we experience music. “When you’re listening to them, you’re not with your friends — at a dinner party listening to sad music,” Houghtaling told Hive. “You’re usually by yourself, and it’s just your connection with the song and the song leaves a lot of things open to your imagination, kind of like a novel, so you can plug in a lot from your life because you’re not given a lot.” But that experience can become complicated by a music video. “When you’re looking at a video, sometimes you’re given a lot of information and you don’t necessarily root yourself as deep into the experience as you would if you’re supplying information that’s a back and forth with your experience and the song.” So we asked Houghtaling to share his top five saddest music videos with us, that give us enough space to dwell in and grieve alongside its characters. Read ‘em and weep.

1. Sinéad O’ Connor, “Nothing Compares 2 U”

Some people think that the worse off you are, the more your body reacts to anything that depresses you. It’s something in the book I refer to as “mirror, mirror, mirror, neurons” and people think that’s how we understand empathy: We mirror the emotional output of people around us. A music video heightens this, especially this one because all you’re doing is looking [Sinéad O’Connor’s] face when she cries. You can’t not engage in some way. The song is amazing and it’s hard to disassociate the video from it.

2. Johnny Cash, “Hurt”

The popular idea of Johnny Cash is “Folsom Prison Blues” and “Ring of Fire.” He’s known as this country outlaw — “the man in black” — but you see him in the [“Hurt”] video almost as exploited. His eyes are so wet and he’s shaking. It was the last single released before he died, and he was literally nearing his death bed. It was captured in such detail that it can’t be anything but heartbreaking. Seeing him in this really intensely, vulnerable place kind of throws off our feeling of him and I think that’s one of the reasons that video is really moving.

3. Radiohead, “All I Need”

The split screen in the video is really dead on and creates the dichotomy of privilege and cruelty and affluence and exploitation and we really hate to acknowledge that kind of stuff in the U.S., and largely we ignore it. The split screen has one kid who’s kind of a Western World kid, on the right, and, on the left, there’s a kid from a Third World Country, who’s the same age. The fact that one kid has been making shoes for a while as the other kid eats breakfast, and keeps making shoes as the Western World kid goes to school and gets out of school, is really, really heartbreaking.

4. The Streets, “Dry Your Eyes”

One of my essays is about songs about the apocalypse and there’s [generally] two different visions for the end of the world: religious and secular. But there’s a third kind — that I really enjoy writing about and playing with — which is the idea that when you break up with somebody, it’s literally the end of the world. It ties into the Streets video because the whole thing is Skinner sitting in these empty, ultraviolet-lit places, like a laundromat. It’s almost post-apocalyptic because everyone else is gone and it’s like he’s the last man on earth. It’s really how it feels when you go through a huge shipwreck kind of breakup. You feel the sense of complete isolation from the rest of the world and that no one understands your pain.

I also love the dog and the great thing about him is that — when you’re in that headspace, you need time to be in that space and — to have something or someone around you who needs to be cared for even though you want to be cared for in that moment is frustrating and heartbreaking in its own kind of way.

5. R.E.M., “Everybody Hurts”

In the same way that we don’t like to be reminded that there’s kids in the Third World making our shoes and soccer balls, we also don’t like to be reminded about how mundane life is — especially in music videos, which are celebrations of emotions usually packed into a few minutes. I love how incredibly mundane this R.E.M. video is and there’s just a bunch of people in traffic. I think we all look around and see all of these people but have no idea who they are and they all have their own complications. Everyone in the video is kind of dying in their own ways. There’s a little kid who wishes his dad would stop singing — which is just the tiniest bit bothersome — and then there’s another person who wishes they had a gun, which is troubling.

This Will End in Tears: The Miserabalists Guide to Music is out now on It Books. You can buy it at Amazon.